Alkyldienamides exhibiting taste and sensory effect in flavor compositions

ABSTRACT

Alkyldienamides compounds suitable for use as flavoring agents are disclosed. The compounds are used as flavors since they possess umami characteristics or other desirable organoleptic properties. The disclosed compounds are defined by the structure set forth below: 
     
       
         
         
             
             
         
       
         
         
           
             wherein R is ethyl or cyclopropyl; and 
             wherein R′ is methyl or butyl, 
             with the proviso that when R is ethyl, R′ is not methyl.

STATUS OF RELATED APPLICATIONS

This application is a divisional of U.S. Ser. No. 10/783,652, filed Feb.20, 2004, now allowed, which is a continuation-in-part of U.S. Ser. No.10/411,672, filed Apr. 11, 2003, now U.S. Pat. No. 7,361,376, each ofwhich is hereby incorporated by reference in its entirety.

FIELD OF THE INVENTION

Alkamide compounds having umami taste and somatosensory attributes inthe oral cavity.

BACKGROUND OF THE INVENTION

The term Umami, from the Japanese word to describe savory or meaty, isthe term used to describe the unique overall fullness, savory orsalivatory taste of food. Materials that exhibit this taste qualitygenerally potentiate the intensity of glutamate solutions and this isone important characteristic of umami taste. It is increasingly becomingrecognized as the fifth sense of taste, the others being sour, sweet,salt and bitter. Compounds traditionally described as possessing thischaracter are monosodium glutamate (MSG), protein hydrolysates, someamino acids and certain nucleotides and phosphates.

MSG is the most widely used material as a “taste enhancer” where itsynergizes the perception of “savory” ingredients, but has also beenalleged to cause allergic reaction to a proportion of the population.Since MSG is widely used in Asian cuisine, especially Chinese, this hasbeen referred to as the Chinese Restaurant Syndrome. Free glutamic acidoccurs in food but this also is the subject of review by The Federationof American Society for Experimental Biology.

Among other chemical compounds several nucleotides have also beendescribed to exhibit the umami effect Adenosine 5′-(trihydrogendiphosphate), 5′-Cytidylic acid (5′-CMP), 5′-Uridylic acid (5′-UMP),5′-Adenylic acid (5′-AMP), 5′-Guanylic acid (5′-GMP), 5′-Inosinic acid(5′-IMP) and the di-sodium salts of 5′-Guanylic acid and 5′-Inosinicacid.

Recent literature cites an extensive range of other organic compounds astaste active components of mixtures shown to give the umami tasteeffect. These include but are not necessarily limited to: organic acidssuch as succinic acid, lactic acid, saturated straight chain aliphaticacids of six, eight, fourteen, fifteen, sixteen, and seventeen carbonchain lengths, Z4,Z7, Z10,Z13,Z16,Z19-docosahexaenoic acid,Z5,Z8,Z11,Z14,Z17-eicosapentaenoic acid, Z9,Z12, Z16,Z19-octadecadienoic acid, Z9-octadecenoic acid, glutaric acid, adipicacid, suberic acid, and malonic acid. Aminoacids having umami effectsreported in the literature include glutamic acid, aspartic acid,threonine, alanine, valine, histidine, proline tyrosine, cystine,methionine, pyroglutamic acid, leucine, lycine, and glycine. Dipeptidespossessing umami properties include Val-Glu and Glu-Asp.

Other miscellaneous compounds having umami properties includealpha-amino adipic acid, malic acid, alpha-aminobutyric acid,alpha-aminoisobutyric acid, E2,E4-hexadienal, E2,E4-heptadienal,E2,E4-octadienal, E2,E4-decadienal, Z4-heptenal, E2,Z6-nonadienal,methional, E3,E5-octadien-2-one, 1,6-hexanediamine, tetramethylpyrazine,trimethylpyrazine, cis-6-dodecen-4-olide and a number of naturallyoccurring amino-acids.

The discovery of alkyldienamides in a wide variety of botanicals and theuse of some of these to impart flavor and/or a sensation is the subjectof a huge amount of literature. Molecules of this type have also beenfound to exhibit biological activity, most notably anti-bacterial,anti-fungal and insecticidal activity. The most significant compounds inthis class, provided with their Chemical Abstract Service number inbrackets are: hydroxy-alpha-sanshool [83883-10-7], alpha-sanshool[504-97-2], hydroxy-epislon-sanshool [252193-26-3], gamma-sanshool[78886-65-4], spilanthol [25394-57-4], N-isobutylE2,E4,8,11-dodecatetraenamide[117824-00-7 and 310461-34-8], isoaffinin[52657-13-3], pellitorine [18836-52-7] and bunganool [117568-40-8] alongwith a small number of geometrical isomers thereof.

Despite these disclosures there is an ongoing need for new flavoringredients particularly those that exhibit advantageous organolepticproperties.

SUMMARY OF THE INVENTION

Our invention relates to novel compounds and a process for augmenting orimparting a taste or somatosensory effect to a foodstuff, chewing gum,medicinal product, toothpaste, alcoholic beverage, aqueous beverage orsoup comprising the step of adding to a foodstuff, chewing gum,medicinal product, toothpaste, alcoholic beverage, aqueous beverage orsoup a taste or sensation augmenting, enhancing or imparting quantityand concentration of at least one N-substituted unsaturated aliphaticalkyl amide defined according to the structure:

wherein X is selected from the group consisting of H, methyl, ethyl,n-propyl, and isopropyl;

Y is selected from the group consisting of methyl, ethyl, cyclopropyl,isopropyl, n-propyl, n-butyl, sec-butyl, isobutyl, 2-methylbutyl, allyl,cyclobutyl,

cyclobutyl, CH₂CH(OH)CH₃, CH(CH₃)CH₂OH, CH₂C(CH₃) OH, CH₂CH₂OH,CH₂CO₂CH₃, gernyl, and neryl;

or X and Y taken together is selected form the group consisting of thestructures:

R³ is selected from the group consisting of methyl and H;

R⁴ is selected from the group consisting of methyl and H;

R⁵ is selected from the group consisting of methyl, phenyl, benzyl,ethyl, propyl, butyl, isopropyl, phenylethyl,

In a highly preferred embodiment of the invention, the amides have thestructure set forth below:

wherein R is selected from the group consisting of methyl, ethyl,n-propyl, isopropyl, cyclopropyl, n-butyl, sec-butyl, isobutyl,cyclobutyl, CH₂CH(CH₃)CH₂CH₃, CH₂CH(OH)CH₃, CH(CH₃)CH₂OH, CH₂C(CH₃)₂OH,CH₂CH₂OH,

cyclopentyl, and allyl; and

wherein R′ is selected from the group consisting of methyl, ethyl,n-propyl, n-butyl, n-pentyl, and n-hexyl.

As used herein these compounds will be referred hereinafter to as“alkyldienamides.”

DETAILED DESCRIPTION OF THE INVENTION

Our invention specifically relates to the novel compositions accordingto the formulas above, which have been described as having the followingflavor characteristics:

Primary Secondary R R′ Compound Characteristic Characteristic CH₂CH₂OHn- N-(2-Hydroxyethyl) Tingle, melon Pepper like butylE2,Z6-dodecadienamide flavor warmth CH₂CH(CH₃)CH₂CH₃ n-N-(2-Methylbutyl) Fruity Salt like butyl E2,Z6-dodecadienamide

Me N-(3,4-Methylenedioxy) benzyl E2,Z6- nonadienamide Numbing TingleCH₂CH(CH₃)CH₂CH₃ Me N-(2-Methylbutyl) Bitter Tingle E2,Z6-nonadienamidecyclopropyl n- N-Cyclopropyl E2,Z6- Fatty Wasabi type butyldodecadienamide mouthfeel burn cyclopropyl Me N-Cyclopropyl E2,Z6- UmamiEnhancement nonadienamide ethyl n- N-Ethyl E2,Z6- MSG like Burning butyldodecadienamide ethyl Me N-Ethyl E2,Z6- Umami Enhancement nonadienamideisobutyl n- N-Isobutyl E2,Z6- Numbing Tingle butyl dodecadienamideisobutyl Me N-Isobutyl E2,Z6- Tingle/ MSG like nonadienamide numbingisopropyl n- N-Isopropyl E2,Z6- Melon/cucumber Tingle butyldodecadienamide Flavor isopropyl Me N-Isopropyl E2,Z6- Cucumber tasteTingle nonadienamide Me Me N-Methyl E2,Z6- Tingle Numbing nonadienamideand uses thereof in augmenting or imparting an olfactory effect orsensation such as a taste or somatosensory effect to a foodstuff,chewing gum, medicinal product, toothpaste, alcoholic beverage, aqueousbeverage or soup, particularly providing a (a) umami taste, (b) tinglesensation, (c) warming/burning sensation, (d) numbing sensation, (e)cooling sensation, and (f) salt effects.

More specifically, examples of the organoleptic properties for thealkyldienamides of our invention are as follows:

Compound Taste and Flavor Characteristics N-(2-Hydroxypropyl) E2,Z6-Cloying, fatty, cod liver oil, fishy. nonadienamide N-(2-Hydroxyethyl)E2,Z6- Strong melon flavor, tingle, burn, dodecadienamide pepper taste.N-(2-Methylbutyl) E2,Z6- Slightly fruity, tingle, salty. dodecadienamideN-(3,4-Methylenedioxy) benzyl Numbing and tingle. E2,Z6-nonadienamideN-(2-Methylbutyl) E2,Z6- Metallic, bitter, tingle. nonadienamideN-Cyclopropyl E2,Z6- Fatty mouthfeel, tongue burn, Wasabidodecadienamide like N-Cyclopropyl E2,Z6- Oily, tingle, strong MSG/umaminonadienamide mouthfeel. N-Ethyl E2,Z6-dodecadienamide Burn, MSG effect,oily flavor, green celery, sweet heating. N-Ethyl E2,Z6-nonadienamideUmami character N-Isobutyl E2,Z6- Some tingle, anesthetic, numbingdodecadienamide effect, interesting cooling/tingle effect, long lasting.The aftertaste is cooling and refreshing. N-Isobutyl E2,Z6- Strongtingle very long lasting, mint, nonadienamide oily, fizzy, tonguenumbing, some MSG effect. N-Isopropyl E2,Z6- Oily flavor, slight tingle.dodecadienamide N-Isopropyl E2,Z6- Oily, cucumber, some tingle, bitter.nonadienamide N-Methyl E2,Z6-nonadienamide Warming, tingle

Other compounds of the present invention include the following:

Name Structure N-Ethyl 3-(cyclohex-3-en-l-yl) E2- propenamide

N-Cyclopropyl 3-(cyclohex-3-en-1-yl) E2-propenamide

N-Ethyl-4-(2,2,3-trimethylcyclopent- 3-en-1-yl) E2-butenamide

N-Cyclopropyl-4-(2,2,3- trimethylcyclopent-3-en-1-yl) E2- butenamide

N-Isopropyl E2,Z6-nonadienamide

N-Ethyl E2,Z6-nonadienamide

N-Methyl E2,Z6-nonadienamide

N-Isobutyl E2,Z6-nonadienamide

N-(2-Methylbutyl) E2,Z6-nonadienamide

N-Cyclopropyl E2,Z6-nonadienamide

N-(2-Hydroxypropyl) E2,Z6- nonadienamide

N-(3,4-Methylenedioxy) benzyl E2,Z6- nonadienamide

N-Allyl E2,Z6-nonadienamide

N-(Carboxymethyl)methyl E2,Z6- nonadienamide

N,N-Dimethyl E2,Z6-nonadienamide

N-Methyl E2,Z6-dodecadienamide

N-Ethyl E2,Z6-dodecadienamide

N-Cyclopropyl E2,Z6-dodecadienamide

N-Isopropyl E2,Z6-dodecadienamide

N-Isobutyl E2,Z6-dodecadienamide

N-(2-Hydroxyethyl) E2,Z6- dodecadienamide

N-(2-Methylbutyl) E2,Z6- dodecadienamide

N-Isobutyl 3,4-(dioxymethylene) cinnamide

Piperidyl 3,4-(dioxymethylene) cinnamide

N,N-Diisopropyl 3-methyl-2-hexenamide

N,N-Dimethyl 3,7-dimethyl-2,6- octadienamide

N-Ethyl 5-phenyl-E2-pentenamide

N,N-Ethyl 3,7-dimethyl-2,6- octadienamide

N-Ethyl 5-phenyl-E2-pentenamide

The literature has not previously reported alkyldienamides having umamiflavor. In addition, closely structurally related compounds such asdienals and unsaturated acids, are not specifically reported to possessumami character when tasted in isolation. In addition the ability toprovide an enhanced saltiness for the product without increasing sodiumlevel is not disclosed or suggested by the prior art. The salt enhancingproperties of the compounds of the present invention are importantbecause it allows flavorists to provide the desired salty taste profilein foods and beverages without actually having higher salt levels in thefood. Therefore the consumer can have both the taste profile that theydesire while without having the adverse health effects associated withincreased salt levels such as hypertension.

As used herein olfactory effective amount is understood to mean theamount of compound in flavor compositions the individual component willcontribute to its particular olfactory characteristics, but the flavor,taste and aroma effect on the overall composition will be the sum of theeffects of each of the flavor ingredients. As used herein taste effectsinclude salt and umami, effects. Thus the compounds of the invention canbe used to alter the taste characteristics of the flavor composition bymodifying the taste reaction contributed by another ingredient in thecomposition. The amount will vary depending on many factors includingother ingredients, their relative amounts and the effect that isdesired.

The level of alkyldienamides used in products is greater than 50 partsper billion, generally provided at a level of from about 50 parts perbillion to about 800 parts per million in the finished product, morepreferably from about 10 parts per million to about 500 parts permillion by weight.

The usage level of alkyldienamides varies depending on the product inwhich the alkyldienamides are employed. For examples, alcoholicbeverages the usage level is from about 1 to about 50 parts per million,preferably from about 5 to about 30 and most preferably from about 10 toabout 25 parts per million by weight. Non-alcoholic beverages areflavored at levels of from about 50 parts per billion to about 5 partsper million, preferably from about 200 parts per billion to about 1 partper million and in highly preferred situations of from about 300 toabout 800 parts per billion. Snack foods can be advantageously flavoredusing alkyldienamides of the present invention at levels of from about10 to about 250 parts per million, preferably from about 50 to about 200and most preferably from about 75 to about 150 parts per million byweight.

Toothpaste can be satisfactorily flavored by using alkyldienamides atlevels of from about 150 to about 500 parts per million, more preferablyfrom about 200 to about 400 parts per million by weight.

Candy products including hard candy can be flavored at levels of fromabout 10 to about 200; preferably from about 25 to about 150 and morepreferably from 50 to 100 parts per million by weight. Gum usage levelsare from about 300 to about 800, preferably from about 450 to about 600parts per million.

The present invention also provides a method for enhancing or modifyingthe salt flavor of a food through the incorporation of anorganoleptically acceptable level of the compounds described herein. Thecompounds can be used individually or in combination with other saltenhancing compounds of the present invention. In addition, the saltenhancing materials of the present invention can be used in combinationwith other salt enhancing compositions known in the art, including butnot limited to cetylpyridium chloride, bretylium tosylate, variouspolypeptides, mixtures of calcium salts of ascorbic acid, sodiumchloride and potassium chloride, as described in various U.S. Pat. Nos.4,997,672; 5,288,510; 6,541,050 and 6,974,597.

The salt taste enhancing compounds of the present invention may beemployed to enhance the perceived salt taste of any salts used in foodor beverage products. The preferred salt taste to be enhanced by thecompounds of the present invention is that of sodium chloride, primarilybecause of the discovery that ingestion of large amounts of sodium mayhave adverse effects on humans and the resultant desirability ofreducing salt content while retaining salt taste.

In addition, the compounds of the present invention may also be employedto enhance the perceived salt taste of known salty tasting compoundswhich may be used as salt substitutes. Such compounds include cationicamino acids and low molecular weight dipeptides. Specific examples ofthese compounds are arginine, hydrochloride, lysine hydrochloride andlysine-ornithine hydrochloride. These compounds exhibit a salty tastebut are typically useful only at low concentrations since they exhibit abitter flavor at higher concentrations. Thus, it is feasible to reducethe sodium chloride content of a food or beverage product by firstformulating a food or beverage with less sodium chloride than isnecessary to achieve a desired salt taste and then adding to said foodor beverage the compounds of the present invention in an amountsufficient to potentiate the salt taste of said salted food or beverageto reach said desired taste. In addition, the sodium chloride contentmay be further reduced by substituting a salty-tasting cationic aminoacid, a low molecular weight dipeptide or mixtures thereof for at leasta portion of the salt.

The salt enhancing level of the compounds of the present invention rangefrom about 100 parts per billion to about 100 parts per million;preferably from about 0.1 parts per million to about 50 parts permillion; and most preferably from about 0.5 parts per million to about10 parts per million when incorporated into the foodstuff.

The term “foodstuff” as used herein includes both solid and liquidingestible materials for man or animals, which materials usually do, butneed not, have nutritional value. Thus, foodstuffs include foodproducts, such as, meats, gravies, soups, convenience foods, malt,alcoholic and other beverages, milk and dairy products, seafood,including fish, crustaceans, mollusks and the like, candies, vegetables,cereals, soft drinks, snacks, dog and cat foods, other veterinaryproducts and the like.

When the alkyldienamides compounds of this invention are used in aflavoring composition, they can be combined with conventional flavoringmaterials or adjuvants. Such co-ingredients or flavor adjuvants are wellknown in the art for such use and have been extensively described in theliterature. Requirements of such adjuvant materials are: (1) that theybe non-reactive with the alkyldienamides of our invention; (2) that theybe organoleptically compatible with the alkyldienamides derivative(s) ofour invention whereby the flavor of the ultimate consumable material towhich the alkyldienamides are added is not detrimentally affected by theuse of the adjuvant; and (3) that they be ingestible acceptable and thusnontoxic or otherwise non-deleterious. Apart from these requirements,conventional materials can be used and broadly include other flavormaterials, vehicles, stabilizers, thickeners, surface active agents,conditioners and flavor intensifiers.

Such conventional flavoring materials include saturated fatty acids,unsaturated fatty acids and amino acids; alcohols including primary andsecondary alcohols, esters, carbonyl compounds including ketones, otherthan the alkyldienamides of our invention and aldehydes; lactones; othercyclic organic materials including benzene derivatives, acycliccompounds, heterocyclics such as furans, pyridines, pyrazines and thelike; sulfur-containing compounds including thiols, sulfides, disulfidesand the like; proteins; lipids, carbohydrates; so-called flavorpotentiators such as monosodium glutamate; magnesium glutamate, calciumglutamate, guanylates and inosinates; natural flavoring materials suchas hydrolyzates, cocoa, vanilla and caramel; essential oils and extractssuch as anise oil, clove oil and the like and artificial flavoringmaterials such as vanillin, ethyl vanillin and the like.

Specific preferred flavor adjuvants include but are not limited to thefollowing: anise oil; ethyl-2-methyl butyrate; vanillin; cis-3-heptenol;cis-3-hexenol; trans-2-heptenal; butyl valerate; 2,3-diethyl pyrazine;methyl cyclo-pentenolone; benzaldehyde; valerian oil;3,4-dimethoxy-phenol; amyl acetate; amyl cinnamate; γ-butyryl lactone;furfural; trimethylpyrazine; phenyl acetic acid; isovaleraldehyde; ethylmaltol; ethyl vanillin; ethyl valerate; ethyl butyrate; cocoa extract;coffee extract; peppermint oil; spearmint oil; clove oil; anethol;cardamom oil; wintergreen oil; cinnamic aldehyde; ethyl-2-methylvalerate; γ-hexenyl lactone; 2,4-decadienal; 2,4-heptadienal; methylthiazole alcohol (4-methyl-5-β-hydroxyethyl thiazole); 2-methylbutanethiol; 4-mercapto-2-butanone; 3-mercapto-2-pentanone;1-mercapto-2-propane; benzaldehyde; furfural; furfuryl alcohol;2-mercapto propionic acid; alkyl pyrazine; methyl pyrazine;2-ethyl-3-methylpyrazine; tetramethylpyrazine; polysulfides; dipropyldisulfide; methyl benzyl disulfide; alkyl thiophene; 2,3-dimethylthiophene; 5-methyl furfural; acetyl furan; 2,4-decadienal; guiacol;phenyl acetaldehyde; β-decalactone; d-limonene; acetoin; amyl acetate;maltol; ethyl butyrate; levulinic acid; piperonal; ethyl acetate;n-octanal; n-pentanal; n-hexanal; diacetyl; monosodium glutamate;monopotassium glutamate; sulfur-containing amino acids, e.g., cysteine;hydrolyzed vegetable protein; 2-methylfuran-3-thiol;2-methyldihydrofuran-3-thiol; 2,5-dimethylfuran-3-thiol; hydrolyzed fishprotein; tetramethylpyrazine; propylpropenyl disulfide; propylpropenyltrisulfide; diallyl disulfide; diallyl trisulfide; dipropenyl disulfide;dipropenyl trisulfide; 4-methyl-2-[(methylthio)-ethyl]-1,3-dithiolane;4,5-dimethyl-2-(methylthiomethyl)-1,3-dithiolane; and4-methyl-2-(methylthiomethyl)-1,3-dithiolane. These and other flavoringredients are provided in U.S. Pat. Nos. 6,110,520 and 6,333,180hereby incorporated by reference.

The alkyldienamides derivative(s) of our invention or compositionsincorporating them, as mentioned above, can be combined with one or morevehicles or carriers for adding them to the particular product. Vehiclescan be edible or otherwise suitable materials such as ethyl alcohol,propylene glycol, water and the like, as described supra. Carriersinclude materials such as gum arabic, carrageenan, xanthan gum, guar gumand the like.

Alkyldienamides prepared according to our invention can be incorporatedwith the carriers by conventional means such as spray-drying, extrusion,drum-drying and the like. Such carriers can also include materials forcoacervating the alkyldienamides of our invention to provideencapsulated products, as set forth supra. When the carrier is anemulsion, the flavoring composition can also contain emulsifiers such asmono- and diglycerides or fatty acids and the like. With these carriersor vehicles, the desired physical form of the compositions can beprepared.

The quantity of alkyldienamides utilized should be sufficient to impartthe desired flavor characteristic to the product, but on the other hand,the use of an excessive amount of alkyldienamides is not only wastefuland uneconomical, but in some instances, too large a quantity mayunbalance the flavor or other organoleptic properties of the productconsumed. The quantity used will vary depending upon the ultimatefoodstuff; the amount and type of flavor initially present in thefoodstuff; the further process or treatment steps to which the foodstuffwill be subjected; regional and other preference factors; the type ofstorage, if any, to which the product will be subjected; and thepreconsumption treatment such as baking, frying and so on, given to theproduct by the ultimate consumer. Accordingly, the terminology“effective amount” and “sufficient amount” is understood in the contextof the present invention to be quantitatively adequate to alter theflavor of the foodstuff.

With reference to the novel compounds of our invention, the synthesis iseffected by means of the reaction of Z4-aldehydes with malonic acidunder pyridine catalysis to furnish the known E2,Z6-acids. Subsequentreaction with ethyl chloroformate in the presence of triethylamine andfurther reaction of the intermediate with amine (added either directlyor in solution) according to the general scheme:

More specifically, with reference to the novel compounds of ourinvention, the synthesis is effected by means of the reaction ofZ4-aldehyde with malonic acid under pyridine catalysis to furnish theknown E2,Z6-acids. Subsequent reaction with ethyl chloroformate in thepresence of triethylamine and further reaction of the intermediate withamine (added either directly or in solution) according to the scheme:

as set forth in examples herein. The acid is dissolved indichloromethane to which ethylchloroformate is added in 1.0 to 2.0equivalents at temperatures ranging from 0° C. to room temperature, mostpreferably from 10° C. to 20° C. The resulting solution is cooled to−10° C. to −30° C., and triethylamine is added in 1.0 to 2.0 equivalentssuch that the temperature range is below 0° C. and the mixture aged for1 hour.

The mixture is filtered, and the filtrate cooled to 0° C. The amine isadded in 1.0 to 7.0 equivalents either neat or as a solution in THF andthe reaction is aged for about 1-3 hours at room temperature.

The reaction can be quenched with aqueous sodium chloride, hydrogenchloride or sodium hydroxide depending of the need to remove residualacid or amine. The mixture is extracted into ethereal solvent ordichloromethane, washed to neutrality and solvent removed.

The crude product is purified by distillation or recrystallizationdepending on the physical properties.

The reaction occurs in 35-75% mole yield based on E2,Z6-acid.

The alkyldienamides of the present invention can be admixed with otherflavoring agents and incorporated into foodstuffs and other productsusing techniques well known to those with ordinary skill in the art.Most commonly the alkyldienamides are simply admixed using the desiredingredients within the proportions stated.

The following are provided as specific embodiments of the presentinvention. Other modifications of this invention will be readilyapparent to those skilled in the art, without departing from the scopeof this invention. As used herein, both specification and followingexamples all percentages are weight percent unless noted to thecontrary.

All U.S. patents cited herein are incorporated by reference as if setforth in their entirety.

Example 1 Preparation of Materials of the Present Invention

The following reaction sequence was used to prepare the specificcompounds described by the NMR data set forth below:

The acid is dissolved in dichloromethane to which ethylchloroformate isadded in 1.0 to 2.0 equivalents at temperatures ranging from 0° C. toroom temperature, most preferably from 10° C. to 20° C. The resultingsolution is cooled to −10° C. to −30° C., and triethylamine is added in1.0 to 2.0 equivalents such that the temperature range is below 0° C.and the mixture aged for 1 hour.

The mixture is filtered, and the filtrate cooled to 0° C. The amine isadded in 1.0 to 7.0 equivalents either neat or as a solution in THF andthe reaction is aged for 1-3 hours at room temperature.

The reaction can be quenched with aqueous sodium chloride, hydrogenchloride or sodium hydroxide depending on the need to remove residualacid or amine. The mixture is extracted into ethereal solvent ordichloromethane, washed to neutrality and solvent removed.

The crude product is purified by distillation or recrystallizationdepending on the physical properties.

The amides are synthesized according to the general scheme above withthe following specific examples. Equivalents set out are moleequivalents based on starting acid, yields are distilled chemical yieldsbased on starting acid.

N-methyl 2E,6Z-nonadienamide

2E,6Z-nonadienoic acid 1 eq, ethyl chloroformate 1.5 eq, triethylamine1.5 eq, methylamine 1.5 eq as a 2.0M solution in THF, quench with 10%sodium chloride solution, yield=47%.

0.95 ppm (t, 3H, J=7.54 Hz, a), 2.02 ppm (quintet, 2H, J=7.33 Hz),

2.19 ppm (m, 4H, c), 2.78 & 2.85 ppm (d, 3H, J=4.81 & 4.87 Hz),

5.27-5.43 ppm (m, 2H, e), 5.90 ppm (d, 1H, J=15.36 Hz),

6.80 ppm (d, 1H, J=15.33 Hz, of t, J=6.59 Hz, g), 6.80 ppm (m, 1H).

N-ethyl 2E,6Z-nonadienamide

2E,6Z-nonadienoic acid 1 eq, ethyl chloroformate 1.5 eq, triethylamine1.5 eq, ethylamine 7.0 eq as a 2.0M solution in THF, quench with 10%hydrogen chloride solution, yield=60%.

0.95 ppm (t, 3H, J=7.55 Hz), 1.16 ppm (t, 3H, J=7.27 Hz),

2.03 ppm (quintet, 2H, J=7.31 Hz), 2.20 ppm (m, 4H),

3.35 ppm (quintet, 2H, J=7.04 Hz), 5.27-5.44 ppm (m, 2H),

5.84 ppm (d, 1H, J=15.32 Hz), 6.16 ppm (br. s, 1H),

6.82 ppm (d, 1H, J=15.28 Hz, of t, J=6.51 Hz).

N-ethyl 2E,6Z-dodecadienamide

2E,6Z-dodecadienoic acid 1 eq, ethyl chloroformate 1.5 eq, triethylamine1.5 eq, ethylamine 7.0 eq as a 2.0M solution in THF, quench with 10%hydrogen chloride solution, yield=65%.

0.89 ppm (t, 3H, J=6.86 Hz), 1.16 ppm (t, 3H, J=7.27 Hz),

1.29 ppm (m, 6H), 2.01 ppm (q, 2H, J=6.79 Hz),

2.20 ppm (m, 4H), 3.35 ppm (m, 2H),

5.30-5.44 ppm (m, 2H), 5.80 ppm (d, 1H, J=15.32 Hz),

5.87 ppm (br. s, 1H), 6.82 ppm (d, 1H, J=15.29 Hz, J=6.61 Hz).

N-isopropyl 2E,6Z-nonadienamide

2E,6Z-nonadienoic acid 1 eq, ethyl chloroformate 1.5 eq, triethylamine1.5 eq, isopropylamine 3.0 eq, quench with 20% sodium chloride,yield=57%.

0.95 ppm (t, 3H, J=7.53 Hz), 1.17 ppm (d, 6H, J=6.59 Hz), 2.03 ppm(quintet, 2H, J=7.36 Hz), 2.19 ppm (m, 4H), 4.14 ppm (m, 1H), 5.27-5.44ppm (m, 2H),

5.83 ppm (d, 1H, J=15.30 Hz), 5.99 ppm (br. s, 1H),

6.81 ppm (d, 1H, J=15.27 Hz, J=6.64 Hz).

N-isopropyl 2E,6Z-dodecadienamide

2E,6Z-dodecadienoic acid 1 eq, ethyl chloroformate 1.5 eq, triethylamine1.5 eq, isopropylamine 3.0 eq, quench with 20% sodium chloride,yield=52%.

0.88 ppm (t, 3H, J=7.53 Hz), 1.18 ppm (d, 6H, J=6.59 Hz), 1.29 ppm (m,6H),

2.02 ppm (q, 2H, J=7.36 Hz), 2.20 ppm (m, 4H), 4.14 ppm (m, 1H),5.27-5.44 ppm (m, 2H), 5.62 ppm (br. s, 1H), 5.78 ppm (d, 1H, J=15.30Hz),

6.79 ppm (d, 1H, J=15.27 Hz, of t, J=6.64 Hz).

N-isobutyl 2E,6Z-nonadienamide

2E,6Z-nonadienoic acid 1 eq, ethyl chloroformate 1.2 eq, triethylamine1.5 eq, isobutylamine 1.0 eq, quench with 10% sodium hydroxide,yield=33%.

0.92 ppm (d, 6H, J=6.74 Hz), 0.95 ppm (t, 3H, J=7.51 Hz), 1.80 ppm(septet, 1H, J=6.73 Hz), 2.03 ppm (quintet, 2H, J=7.27 Hz), 2.20 ppm (m,4H), 3.14 ppm (t, 2H, J=6.53 Hz), 5.28-5.47 ppm (m, 2H), 5.85 ppm (d,1H, J=15.29 Hz), 5.88 ppm (br. s, 1H), 6.82 ppm (d, 1H, J=15.27 Hz, oft, J=6.61 Hz).

N-isobutyl 2E,6Z-dodecadienamide

2E,6Z-dodecadienoic acid 1 eq, ethyl chloroformate 1.2 eq, triethylamine1.5 eq, isobutylamine 3.0 eq, quench with 10% hydrogen chloridesolution, yield=41%.

0.88 ppm (t, 3H, J=6.99 Hz), 0.92 ppm (d, 6H, J=6.70 Hz), 1.29 ppm (m,6H),

1.80 ppm (m, 1H, J=6.73 Hz), 2.01 ppm (q, 2H, J=6.75 Hz), 2.20 ppm (m,4H),

3.14 ppm (t, 2H, J=6.47 Hz), 5.30-5.44 ppm (m, 2H), 5.84 ppm (d, 1H,J=15.30 Hz), 5.97 ppm (m, 1H), 6.82 ppm (d, 1H, J=15.28 Hz, of t, J=6.55Hz).

N-(2-methylbutyl) 2E,6Z-nonadienamide

2E,6Z-nonadienoic acid 1 eq, ethyl chloroformate 1.5 eq, triethylamine1.5 eq, 2-methylbutylamine 3.0 eq, quench with 20% sodium chloride,yield=37%.

0.90 ppm (d, 3H, J=6.57 Hz), 0.90 ppm (t, 3H, J=7.45 Hz), 0.96 ppm (t,3H, J=7.55 Hz), 1.17 ppm (m, 1H), 1.42 ppm (m, 1H), 1.58 ppm (m, 1H),2.03 ppm (quintet, 2H, J=7.33 Hz), 2.20 ppm (m, 4H), 3.09-3.29 ppm (m,2H), 5.28-5.44 ppm (m, 2H), 5.80 ppm (br. s, 1H), 5.82 ppm (d, 1H,J=15.34 Hz), 6.82 ppm (d, 1H, J=15.23 Hz, of t, J=6.55 Hz).

N-(2-methylbutyl) 2E,6Z-dodecadienamide

2E,6Z-dodecadienoic acid 1 eq, ethyl chloroformate 1.5 eq, triethylamine1.5 eq, 2-methylbutylamine 3.0 eq, quench with 20% sodium chloride,yield=45%.

0.7-0.92 ppm (m, 9H), 1.17 ppm (m, 1H), 1.29 ppm (m, 6H), 1.36 ppm (m,1H),

1.57 ppm (m, 1H), 2.01 ppm (q, 2H, J=6.82 Hz), 2.20 ppm (m, 4H),3.09-3.29 ppm (m, 2H), 5.30-5.44 ppm (m, 2H), 5.82 ppm (br. s, 1H),

5.83 ppm (d, 1H, J=15.27 Hz), 6.82 ppm (d, 1H, J=15.26 Hz, of t, J=6.58Hz).

N-cyclopropyl 2E,6Z-nonadienamide

2E,6Z-nonadienoic acid 1 eq, ethyl chloroformate 1.5 eq, triethylamine1.5 eq, cyclopropylamine 2.0 eq, quench with 10% hydrogen chloridesolution, yield=49%.

0.53 ppm (m, 2H), 0.77 ppm (m, 2H), 0.95 ppm (t, 3H, J=7.53 Hz), 2.02ppm (quintet, 2H, J=7.37 Hz), 2.19 ppm (m, 4H), 2.77 ppm (m, 1H),

5.26-5.43 ppm (m, 2H), 5.79 ppm (d, 1H, J=15.30 Hz), 6.15 ppm (br. s,1H),

6.82 ppm (d, 1H, J=15.30 Hz, of t, J=6.58 Hz).

N-cyclopropyl 2E,6Z-dodecadienamide

2E,6Z-dodecadienoic acid 1 eq, ethyl chloroformate 1.5 eq, triethylamine1.5 eq, cyclopropylamine 2.4 eq, quench with 10% hydrogen chloridesolution, yield=55%.

0.53 ppm (m, 2H), 0.76 ppm (m, 2H), 0.88 ppm (t, 3H, J=6.85 Hz), 1.29ppm (m, 6H), 2.00 ppm (q, 2H, J=6.80 Hz), 2.18 ppm (m, 4H), 2.78 ppm (m,1H), 5.29-5.43 ppm (m, 2H), 5.83 ppm (d, 1H, J=15.34 Hz),

6.46 ppm (br. s, 1H), 6.82 ppm (d, 1H, J=15.30 Hz, of t, J=6.52 Hz).

N-(2-hydroxyethyl) 2E,6Z-dodecadienamide

2E,6Z-dodecadienoic acid 1 eq, ethyl chloroformate 1.5 eq, triethylamine1.5 eq, 2-ethanolamine 3.0 eq, quench with 20% sodium chloride andwashed with dilute hydrogen chloride solution, yield=48%.

0.89 ppm (t, 3H, J=7.05 Hz), 1.29 ppm (m, 6H), 2.01 ppm (q, 2H, J=7.01Hz),

2.20 ppm (m, 4H), 3.47 ppm (m, 2H), 3.73 ppm (m, 2H), 4.17-4.28 ppm (br.m, 1H), 5.29-5.44 ppm (m, 2H), 5.84 ppm (d, 1H, J=15.37 Hz), 6.43-6.47ppm (br. m, 1H), 6.84 ppm (d, 1H, J=15.31 Hz, of t, J=6.54 Hz).

N-(3,4-methylenedioxy)benzyl 2E,6Z-nonadienamide

2E,6Z-nonadienoic acid 1 eq, ethyl chloroformate 1.5 eq, triethylamine1.5 eq, piperonylamine 1.5 eq, quench with 10% sodium hydroxidesolution, re-crystallized from hexane, yield=72%.

0.95 ppm (t, 3H, J=7.53 Hz), 2.03 ppm (quintet, 2H, J=7.37 Hz), 2.20 ppm(m, 4H),

4.39 ppm (d, 2H, J=5.76 Hz), 5.27-5.44 ppm (m, 2H), 5.76 ppm (br. s,1H),

5.78 ppm (d, 1H, J=15.38 Hz), 5.94 ppm (s, 2H), 6.75-6.79 ppm (m, 3H),

6.86 ppm (d, 1H, J=15.27 Hz, of t, J=6.59 Hz).

N-ethyl 3-(3-cyclohexenyl)-2E-propenamide

3-(3-Cyclohexenyl)-2E-propenoic acid 1 eq, ethyl chloroformate 1.5 eq,triethylamine 1.5 eq, ethylamine 1.5 eq as a 2.0M solution in THF,quench with 10% sodium chloride solution, yield=39%.

1.17 ppm (t, 3H, J=7.25 Hz), 1.45 ppm (m, 1H), 1.80-1.83 ppm (m, 1H),1.88-1.94 ppm (m, 1H), 2.09 ppm (m, 3H), 2.41 ppm (br. s, 1H), 3.36 ppm(m, 2H), 5.68 ppm (br. s, 3H), 5.77 ppm (d, 1H, J=15.40 Hz), 6.83 ppm(d, 1H, J=15.39 Hz, of d, J=7.02 Hz)

N-cyclopropyl 3-(3-cyclohexenyl)-2E-propenamide

3-(3-Cyclohexenyl)-2E-propenoic acid 1 eq, ethyl chloroformate 1.5 eq,triethylamine 1.5 eq, cyclopropylamine 1.6 eq, quench with 10% sodiumchloride solution, yield=69%.

0.53 ppm (d, 2H, J=1.96 Hz), 0.79 ppm (d, 2H, J=5.59 Hz), 1.44 ppm (m,1H), 1.82 ppm (m, 1H), 1.93 ppm (m, 1H), 2.08 ppm (m, 3H), 2.40 ppm (br.s, 1H), 2.78 ppm (m, 1H), 5.68 ppm (s, 2H), 5.73 ppm (d, 1H, J=15.58Hz), 5.82 ppm (br. s, 1H), 6.84 ppm (d, 1H, J=15.41 Hz, of d, J=7.02 Hz)

N-allyl 2E,6Z-nonadienamide

2E,6Z-Nonadienoic acid 1 eq, ethyl chloroformate 1.5 eq, triethylamine1.5 eq, allylamine 1.5 eq, quench with 10% sodium chloride solution,yield=58%.

0.95 ppm (t, 3H, J=7.560 Hz), 2.03 ppm (quintet, 2H, J=7.37 Hz),2.18-2.23 ppm (m, 4H), 3.93 ppm (t, 2H, J=5.59 Hz), 5.16 ppm (d, 2H,J=17.14 Hz, of d, J=10.23 Hz), 5.30-5.43 ppm (m, 2H), 5.83-5.89 ppm (m,1H), 5.86 ppm (d, 1H, J=14.02 Hz), 6.10 ppm (br. s, 1H), 6.81-6.86 ppm(d, 1H, J=15.29 Hz, of t, J=6.52 Hz)

N-allyl 3-methyl-2E-butenamide

3-Methyl-2E-butenoic acid 1 eq, ethyl chloroformate 1.5 eq,triethylamine 1.5 eq, allylamine 1.5 eq, quench with 10% sodium chloridesolution, yield=46%.

1.83 ppm (s, 3H), 2.16 ppm (s, 3H), 3.90 ppm (t, 2H, J=5.63 Hz, of d,J=1.43 Hz), 5.11 ppm (t, 1H, J=10.22 Hz, of d, J=1.35 Hz), 5.18 ppm (t,1H, J=17.15 Hz, of d, J=1.48 Hz),

5.62 ppm (s, 1H), 5.81-5.89 ppm (m, 1H), 5.96 ppm (br. s, 1H)

N,N,3,7-tetramethyl-2E,6-octadienamide

3,7-Dimethyl-2E,6-octadienoic acid 1 eq, ethyl chloroformate 1.5 eq,triethylamine 1.5 eq, dimethylamine 1.5 eq as a 40 wt % solution inwater, quench with 10% sodium chloride solution, yield=46%.

1.61 ppm (s, 3H), 1.68 ppm (s, 3H), 1.86 ppm (2s, 3H), 2.13-2.16 ppm (m,3H), 2.34 ppm (t, 1H, J=7.76 Hz), 2.96-3.01 ppm (m, 6H), 5.11 ppm (m,1H), 5.78 ppm (m, 1H)

N-(carbomethoxy)methyl 2E,6Z-nonadienamide

2E,6Z-Nonadienoic acid 1 eq, ethyl chloroformate 1.5 eq, triethylamine1.5 eq, glycine 1.5 eq, quench with 10% sodium chloride solution,yield=62%.

0.96 ppm (t, 3H, J=7.53 Hz), 2.03 ppm (quintet, 2H, J=7.45 Hz), 2.19 ppm(t, 2H, J=6.44 Hz), 2.23 ppm (t, 2H, J=6.28 Hz), 3.75 ppm (s, 3H), 4.10ppm (d, 2H, J=5.41 Hz), 5.31 ppm (m, 1H), 5.39 ppm (m, 1H), 5.91 ppm (d,1H, J=15.37 Hz), 6.60 ppm (br. s, 1H), ppm (d, 1H, J=15.33 Hz, of t,J=6.57 Hz)

N-ethyl 4-(2,2,3-trimethyl-3-penten-1-yl)-2E-butenamide

4-(2,2,3-Trimethyl-3-penten-1-yl)-2E-butenoic acid 1 eq, ethylchloroformate 1.5 eq, triethylamine 1.5 eq, ethylamine 1.5 eq as a 2.0Msolution in THF, quench with 10% sodium chloride solution, yield=22%.

0.79 ppm (s, 3H), 0.99 ppm (s, 3H), 1.17 ppm (t, 3H, J=7.27 Hz), 1.60ppm (s, 3H), 1.81-1.92 ppm (m, 2H), 2.07-2.13 ppm (m, 1H), 2.27-2.35 ppm(m, 2H), 3.36 ppm (q, 2H, J=7.22 Hz, of d, J=7.79 Hz), 5.22 ppm (s, 1H),5.37 ppm (br. s, 1H), 5.77 ppm (d, 1H, J=15.20 Hz), 6.83 ppm (d, 1H,J=15.19 Hz, of t, J=7.31 Hz)

N-cyclopropyl 4-(2,2,3-trimethyl-3-penten-1-yl)-2E-butenamide

4-(2,2,3-Trimethyl-3-penten-1-yl)-2E-butenoic acid 1 eq, ethylchloroformate 1.5 eq, triethylamine 1.5 eq, cyclopropylamine 1.5 eq,quench with 10% sodium chloride solution, yield=40%.

0.53 ppm (m, 90% of 2H), 0.62 ppm (m, 10% of 2H), 0.79 ppm (s, 3H), 0.80ppm (m, 2H), 0.99 ppm (s, 3H), 1.60 ppm (s, 3H), 1.80-1.91 ppm (m 2H),2.06-2.12 ppm (m, 1H),

2.30 ppm (m, 2H), 2.78 ppm (m, 1H), 5.21 ppm (s, 1H), 5.58 ppm (br. s,1H), 5.74 ppm (d, 1H, J=15.20 Hz), 6.84 ppm (d, 1H, J=15.20 Hz, of t,J=7.31 Hz)

N,N-dimethyl 2E,6Z-Nonadienamide

2E,6Z-Nonadienoic acid 1 eq, ethyl chloroformate 1.5 eq, triethylamine1.5 eq, dimethylamine 1.5 eq as a 40 wt % solution in water, quench with10% sodium chloride solution, yield=63%.

0.96 ppm (t, 3H, J=7.53 Hz), 2.04 ppm (quintet, 2H, J=7.41 Hz),2.18-2.28 ppm (m, 4H), 2.99 ppm (s, 3H), 3.07 ppm (s, 3H), 5.29-5.43 ppm(m, 2H), 6.26 ppm (d, 1H, J=15.10 Hz), 6.82-6.88 (d, 1H, 15.09 Hz, of d,J=6.72 Hz)

N-ethyl 5-phenyl-2E-pentenamide

5-Phenyl-2E-pentenoic acid 1 eq, ethyl chloroformate 1.5 eq,triethylamine 1.5 eq, ethylamine 1.5 eq as a 2.0M solution in THF,quench with 10% sodium chloride solution, yield=39%.

1.15 ppm (t, 3H, J=7.27 Hz), 2.49 ppm (m, 2H), 2.75 ppm (t, 2H, J=7.80Hz), 3.34 ppm (q, 2H, J=7.24 Hz, of d, J=1.53 Hz), 5.60 ppm (br. s, 1H),5.77 ppm (t, 1H, J=15.28 Hz, of t, J=1.52 Hz), 6.87 ppm (t, 1H, J=15.27Hz, of t, J=6.87 Hz), 7.16-7.20 ppm (m, 3H), 7.26-7.29 ppm (m, 2H)

N-cyclopropyl 5-phenyl-2E-pentenamide

5-Phenyl-2E-pentenoic acid 1 eq, ethyl chloroformate 1.5 eq,triethylamine 1.5 eq, cyclopropylamine 1.5 eq, quench with 10% sodiumchloride solution, yield=85%.

N-ethyl 2E,6Z-dodecadienamide

2E,6Z-dodecadienoic acid 1 eq, ethyl chloroformate 1.5 eq, triethylamine1.5 eq, methylamine 5.0 eq as a 2.0M solution in THF, quench with 10%hydrogen chloride solution, yield=59%.

N-ethyl 3,7-dimethyl-2E,6-octadienamide

3,7-Dimethyl-2E,6-octadienoic acid 1 eq, ethyl chloroformate 1.5 eq,triethylamine 1.5 eq, ethylamine 3.05 eq as a 70 wt % solution in water,quench with 10% sodium chloride solution, yield=51%.

N,N-Diisopropyl-3-methyl-2E-hexenamide

3-Methyl-2E-hexenoic acid 1 eq, ethyl chloroformate 1.5 eq,triethylamine 1.6 eq, diisopropylamine 3.0 eq, quench with 10% hydrogenchloride solution, yield=34%.

Example 2 Preparation of Non-Alcoholic Beverage Flavor System

A non-alcoholic beverage formulation was prepared according to thefollowing formulation.

Water 866.82 grams High Fructose Corn Syrup 55  129.8 grams (77° Brix)Citric Acid  3.38 grams

The flavor applied to the beverages consisted of a blend of single foldlemon oil and distilled lime oil. The control beverage contained 35 PPMof this flavor. This control beverage exhibited the tastecharacteristics of a tart lemon lime flavor. Another beverage wasprepared containing 35 PPM of the same flavor and 0.5 PPM of N-EthylE2,Z6-nonadienamide. This beverage exhibited enhanced flavor impact,increased tartness, and an increased perception of freshness as well asit being described as having a more “natural” flavor.

Example 3 Preparation of an Alcoholic Beverage Flavor System

Flavored beverages were prepared using the following 30° Proof alcoholicbase:

190° Proof food grade Ethyl 157.89 milliliters Alcohol High FructoseCorn Syrup 55 217.00 milliliters (77° Brix) Citric Acid (50% solution) 3.00 milliliters Water 622.11 milliliters

The peach flavor applied to the beverages consisted of a blend of GammaDecalactone, Benzaldehyde, Cis-3-hexenol, Butyric acid, 2-Methyl butyricacid, Iso butyl acetate, Linalool, and para-Mentha-8-thiol-3-one. Thecontrol beverage contained 60 PPM of the above flavor blend. Thiscontrol beverage exhibited the taste characteristics of a mild candiedgreen peach. Another beverage was prepared containing 60 PPM of the sameflavor and 20 PPM of N-(3,4-methylenedioxy) benzyl E2,Z6-nonadienamide.This beverage exhibited an enhanced perception of alcohol, increasedflavor impact, and a tingle effect on the tongue.

Example 4 Preparation of a Toothpaste Product

The following separate groups of ingredients were prepared:

Group “A”

Ingredients weight Percent glycerin 30.2 distilled water 15.3 sodiumbenzoate 0.1 sodium saccharin 0.2 stannous flouride 0.5

Group “B”

Ingredients Weight Percent calcium carbonate 12.5 dicalcium phosphate37.2 (dihydrate)

Group “C”

2.0 parts by weight of sodium n-Lauroyl sarcosinate (foaming agent)

Group “D”

1.0 parts by weight of the flavor material which is a blend ofpeppermint oil, spearmint oil, anethole, and menthol.

Procedure:

-   (1) The ingredients in Group “A” were stirred and heated in a steam    jacketed kettle to 160° F.-   (2) Stirring was continued for an additional 3 to 5 minutes to form    a homogeneous gel.-   (3) The powders of Group “B” were added to the gel, while mixing    until a homogeneous paste is formed.-   (4) With stirring, the flavor of Group “D” was added, followed by    addition immediately thereafter of the foaming agent of Group “C”.-   (5) The resultant slurry was then blended for one hour.

The completed paste was then transferred to a three-roller mill,homogenized and finally tubed. The resulting toothpaste when used in anormal tooth brushing procedure yields a slightly bitter/medicinal mintflavor which exhibits moderate cooling. To this control paste 200 ppm ofN-Isobutyl E2,Z6-dodecadienamide is added. This toothpaste exhibitsmoderate cooling without the bitterness of the control sample. Inaddition, the sample exhibited tingle on the tongue and a slight numbingon the lips.

Example 5 Preparation of a Chewing Gum Flavor

100 parts by weight of vehicle were mixed with 5 parts by weight ofbubble gum flavor which is a blend of orange oil, amyl acetate, clovebud oil, ethyl butyrate, and methyl salicylate. To this 300 partssucrose and 100 parts corn syrup were added. Mixing was effected in aribbon blender with jacketed sidewalls of the type manufactured by BakerPerkins Co. The resultant chewing gum blend was then manufactured intostrips 1 inch in width and 0.1 inches in thickness. These strips werecut into lengths of 3 inches each. This control gum exhibited a fruitycitrus spice flavor when chewed. Another gum sample was prepared usingthe above recipe with the addition of 0.25 parts of N-IsobutylE2,Z6-nonadienamide. The resulting gum had a similar taste profile tothe control gum, however, it exhibited a pleasant tingle effect whenchewed.

Example 6 Preparation of Flavor for Use in Hard Candy

Sugar 137 grams  Corn Syrup 42 DE 91 grams Water 46 grams

The above ingredients were added to a stainless steel pot. With constantmixing the ingredients were brought to 295° F. The pot was removed fromthe heat and 0.5 grams of cinnamon bark oil was blended in. This liquidcandy was then deposited into molds where it was left to cool. Thisrecipe yielded 200 grams of finished candy. The resulting control candyexhibited a cinnamon bark type flavor with low to moderate warmth.Another candy sample was prepared using the above recipe with theaddition of 100 PPM of N-Methyl E2,Z6-nonadienamide. This candyexhibited a greener flavor with less warmth, a slight numbing and amoderate level of tingle.

Example 7 Use of the Compounds as Salt Enhancer

A trained consumer panel evaluated a series of molecules set forth belowin a tasting solutions and were asked to rate the perception of thesalty and umami character of each taste solution. The molecules employedin the test were:

-   2,6-Nonadienamide,N-2-Propenyl-,(2E,6Z)-   2,6-Dodecadienamide,N-Ethyl-(2E,6Z)-   N-Isobutyl-(E2,Z6)-Nonadienamide-   (6Z,2E)-N-(2-Hydroxyethyl)dodeca-2,6-dienamide-   (6Z,2E)-n-(methylethyl)nona-2,6-dienamide-   2,6-Nonadienamide,N-ethyl-,(2E,6Z)-   (2E)-N,N,3,7-Tetramethylocta-2,6-dienamide-   2-Propenamide,3-(3-cyclohexen-1-yl)-N-ethyl-,(2E)-   2,6-Dodecadienamide,N-cyclopropyl-,(2E,6Z)-   (6Z,2E)-N-(methylethyl)dodeca-2,6-dienamide-   n-Cyclopropyl-E2,Z6)-Nonadienamide-   2-Propenamide,3-(2-cyclohexen-1-yl)-n-cyclopropyl-,(2E)

The taste solutions presented to the panelists contained 0.3% by weightNaCl, and varying amounts of monosodium glutamate and Ribotides (acommercially available blend of disodium guanylate and disodiuminosinate). The MSG content of the taste solutions varied from 0 to0.18% by weight and the Ribotides varied from 0% to 0.013% by weight.The molecules of this invention were added to the tasting solution inamounts varying between 0 to 1.3 parts per million by weight.

The taste panel found the molecules of the invention increased theperception of saltiness as much as 40% and a smaller but stillsignificant increase in the umami perception of up to 17%.

The panel of flavorists and food technologists were asked to evaluate aseries of reduced sodium chicken broth versus a full sodium chickenbroth. In this degree of difference testing, the panel was able to finda significant difference in the taste of chicken broth containing 10%less salt. The panel found the difference in the taste of the low saltsample to be pronounced when the salt was reduced by 15%.

Samples of lower salt chicken broth containing 800 parts per billion ofthe molecules of the invention provided above were given to this panelfor evaluation. The panel could not perceive the difference between thefull salt chicken broth and the chicken broth with 15% less saltcontaining the molecules set forth above. A sample of broth containingmolecules of this invention with a 20% reduction in salt was notperceived as significantly different from the full salt broth.

A commercially available rice side dish was prepared with and withoutthe addition of molecules listed above. These molecules were added at 5and 10 ppm to the prepared rice mix. The rice mix was then prepared onthe stove top according to the directions on the package. A panel offlavorists and food technologists were asked to rate the saltiness orthe samples. The panel found that the rice samples with the addition ofthe molecules were significantly saltier than the unflavored reference.

The molecules of this invention were added to a range of dairyproducts—yoghurt, sour cream, skim milk and full fat milk. The moleculeswere added in levels ranging from 1 to 5 ppm to the finished dairyproduct. A panel of flavorists and food technologists were presented theflavored and unflavored samples blind and asked to comment on the tastedifferences. The dairy samples containing the molecules were uniformlyrated as creamier and more fatty tasting than the unflavored samples.

1. A compound having a structure:

wherein R is ethyl or cyclopropyl; and wherein R′ is methyl or butyl,with the proviso that when R is ethyl, R′ is not methyl.
 2. A compoundN-cyclopropyl E2,Z6-nonadienamide.
 3. A process for augmenting,enhancing, or imparting a taste or somatosensory effect to a foodstuffor a beverage, said process comprising the step of adding a taste orsensation augmenting, enhancing, or imparting level of a compound havinga structure:

wherein R is ethyl or cyclopropyl; and wherein R′ is methyl or butyl,with the proviso that when R is ethyl, R′ is not methyl.
 4. The processof claim 3, wherein the compound is N-cyclopropyl E2,Z6-nonadienamide.5. The process of claim 3, wherein the level is greater than about 50parts per billion by weight.
 6. The process of claim 3, wherein thelevel is from about 100 parts per billion to about 100 parts per millionby weight.
 7. A foodstuff comprising the compound of claim
 1. 8. Afoodstuff comprising the compound of claim
 2. 9. A beverage comprisingthe compound of claim
 1. 10. A beverage comprising the compound of claim2.